Where casino kingpins, software top dogs, and the super-rich go to play

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This year has been a life-altering one for casino impresario Steve Wynn: the opening of his new Vegas resort, a divorce from his wife, and selling his Fifth Avenue apartment. Still, Wynn has found time to enjoy the good life. In the spring, he celebrated a spry 67th birthday at the famously posh ski resort town of St. Moritz, Switzerland.

Although all the billionaires on Forbes' list of the 400 Richest Americans can afford the best suite at any luxury hotel, it seems that the hottest commodity among the wealthy is a portfolio of amazing homes in the places they like to visit the most. And when it's not a home, it's the next best thing—a yacht.

Sellers of super-expensive properties and yacht brokers have felt the economy’s woes, but recession-proof moguls like Rupert Murdoch and Hollywood bigwigs like Steven Spielberg still enjoy the privacy, or see the innate investment opportunity in owning their playgrounds and playthings. Many more of the Richest Americans are still visiting their sprawling ranches and floating on their mega yachts—not to mention buying, selling and upgrading their properties as if they were securities.

Designer extraordinaire Ralph Lauren has no fewer than five residences—each one a classic getaway, like the breezy Round Hill villa in Jamaica and the rugged 15,000-acre Colorado ranch. Donald Trump's Mar-a-Lago estate in Palm Beach has once again become his preferred vacation spot following last year's jaw-dropping $100-million sale of another Palm Beach home.

New York City mayor Michael Bloomberg spends time at his residence in Vail, Colo., where he frequently dines at Vail Mountain’s exclusive Game Creek Club—for which members pay an exorbitant $50,000 initiation fee. The Vail chalet complements his home in Tucker's Town, Bermuda; the $10 million Victorian townhouse in London's Cadogan Square; and the sprawling Westchester estate in Armonk, N.Y. When he heads to Bermuda, the billionaire politician, an avid golfer, hits the links along with neighbors and fellow scions-turned-politicos, Ross Perot and Silvio Berlusconi, both of whom also reside in the "millionaire's row" private enclave of Tucker's Town.

“Aside from the obvious—breathtaking views, turquoise water, pink sand beaches—Tucker’s Town offers exclusivity,” says Kelly Petrone, public relations account supervisor for the Bermuda Board of Tourism. “Access to the primarily residential area is restricted. Residents and invited guests must first pass by a guard house. People who do not live in Tucker's Town are not generally allowed in the eastern part of the town, or onto the Tucker's Town Peninsula which extends along the southeastern edge of Castle Harbor.” In this case, it's not just convenience that's king, it's confidentiality.

But not all billionaires are sitting at home, twiddling their Midas fingers. Media tycoon Rupert Murdoch set out upon a deep sea adventure this year, taking friends and family on a cruise to Alaska aboard his 183-foot monster sailboat, The Rosehearty, which is outfitted with all the comforts of home: an on-board “technogym,” deep-sea diving gear, plush king-size sleeping cabin and extravagant interiors designed by minimalist French designer Christian Liaigre. Likewise, Steven Spielberg explored Ireland on a spiritual David Whyte tour, zigzagging through the country’s natural wonders. Spielberg listened to poetry on jagged cliffs of the Aran Islands, soaked up quiet village life while in the Burren, and toured the moors in a souped-up motorized bike.

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The richest man in America seeks waterfront views all over the world. This summer, Bill Gates, with his wife Melinda, cruised along the Dalmatian Coast on a luxury yacht. The pair docked to see waterfalls on the Croatian island Krk and to sightsee at Skradin, an ancient mainland village.

The most famous woman on the Forbes 400, Oprah Winfrey, also headed for Europe recently, with 1,700 of her employees and their families in tow. The group took over shops and restaurants at Barcelona's Poble Espanyol, a full reconstruction of an old Spanish village, and she watched flamenco dancers and concerts with her guests. The after-party? A 10-day Mediterranean cruise, hopping from Italy to Greece, Turkey and Malta, all expenses paid by the star.

A handful of the billionaires found their sea legs this year: Las Vegas hotel magnate Steve Wynn enjoyed his recent purchase, a 183-foot yacht, in Caribbean waters, where he rang in the New Year. Larry Ellison brought The Rising Sun, his $200-million megayacht co-owned with Rich List-mate David Geffen, Stateside and docked in the elite New England vacation spot, Newport, R.I. Even Bill Gates came on board, sailing the Adriatic Sea where he and his family checked out waterfalls on the Croatian island Krk and went sightseeing in Skradin, an ancient mainland village.

Though you may not get there in a MiG 29 like Ellison or jumbo sailboat like Murdoch, many of the rich on our list have favorite vacation spots that aren't so exotic—from Aspen to Montauk—that they visit time and time again, and where you too can have yourself a rich old time.